This paper argues that, as we move towards a ‘post-digital’ world where use of the Web becomes normalised, there is a need to address Web accessibility measurement challenges within a wider real-world context. Strategy and policy that defines Web accessibility purely by the conformance of digital resources with technical guidelines can lead to a danger that ‘good enough’ solutions may fail to be deployed; they also fail to consider a wider measure of user experience in accessibility measurement. We propose that metrics should draw on aspects of user experience to provide a more meaningful, real-world measure of the impact (or not) of accessibility barriers and therefore priority in addressing them. Metrics should also consider context in terms of the quality of effort taken by organisations to provide an inclusive experience; one option for doing so is the framework provided by British Standard 8878 Code of Practice for Web Accessibility. In both cases, challenges exist in the complexity of defining and implementing such metrics.